DE60302061D1 - MICROBIAL N- AND O-DEMETHYLATION OF THE THEBIN DERIVATIVE - Google Patents
MICROBIAL N- AND O-DEMETHYLATION OF THE THEBIN DERIVATIVEInfo
- Publication number
- DE60302061D1 DE60302061D1 DE60302061T DE60302061T DE60302061D1 DE 60302061 D1 DE60302061 D1 DE 60302061D1 DE 60302061 T DE60302061 T DE 60302061T DE 60302061 T DE60302061 T DE 60302061T DE 60302061 D1 DE60302061 D1 DE 60302061D1
- Authority
- DE
- Germany
- Prior art keywords
- cunninghamella
- demethylation
- derivative
- nrrl
- thebin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000010520 demethylation reaction Methods 0.000 title abstract 3
- 230000000813 microbial effect Effects 0.000 title 1
- 241001290628 Cunninghamella echinulata Species 0.000 abstract 5
- 238000000034 method Methods 0.000 abstract 2
- 241000235555 Cunninghamella Species 0.000 abstract 1
- 241000293023 Cunninghamella polymorpha Species 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- 241000235546 Rhizopus stolonifer Species 0.000 abstract 1
- 239000011942 biocatalyst Substances 0.000 abstract 1
- 238000000855 fermentation Methods 0.000 abstract 1
- 230000004151 fermentation Effects 0.000 abstract 1
- FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical class C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/09—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems
- C07D489/10—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14
- C07D489/12—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14 the bridge containing only two carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a process for the N-demethylation or the N- and O-demethylation of a thebaine derivative which process comprises fermenting the derivative with a biocatalyst selected from the filamentous fungi from Cunninghamella dalmatica NRRL 1394, Cunninghamella echinulata NRRL 1387, Cunninghamella echinulata NRRL 1384, Cunninghamella echinulata ATCC 36190, Cunninghamella echinulata ATCC 11585a, Cunninghamella echinulata ATCC 9244, Cunninghamella polymorpha NRRL 1395, or Rhizopus nigricans Z5/1 in a basal fermentation medium at a temperature of at least 25° C. and not more than 34° C., for a period of time of at least 3 days.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0210638 | 2002-05-10 | ||
| GB0210638A GB2388369B (en) | 2002-05-10 | 2002-05-10 | Demethylation of thebaine derivative |
| PCT/GB2003/001735 WO2003095458A1 (en) | 2002-05-10 | 2003-04-24 | Microbial n- and o-demethylation of a thebaine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60302061D1 true DE60302061D1 (en) | 2005-12-01 |
| DE60302061T2 DE60302061T2 (en) | 2006-07-27 |
Family
ID=9936365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60302061T Expired - Lifetime DE60302061T2 (en) | 2002-05-10 | 2003-04-24 | MICROBIAL N- AND O-DEMETHYLATION OF THE THEBIN DERIVATIVE |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7267968B2 (en) |
| EP (1) | EP1504011B1 (en) |
| AT (1) | ATE307816T1 (en) |
| AU (2) | AU2003226563A1 (en) |
| CA (1) | CA2484985C (en) |
| DE (1) | DE60302061T2 (en) |
| ES (1) | ES2252687T3 (en) |
| GB (1) | GB2388369B (en) |
| WO (1) | WO2003095458A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8232398B2 (en) * | 2008-09-30 | 2012-07-31 | Mallinckrodt Llc | Recycling process for increasing the yield of opiate alkaloid derivatives |
| US8227608B2 (en) * | 2008-09-30 | 2012-07-24 | Mallinckrodt Llc | Processes for increasing the yield of opiate alkaloid derivatives |
| AU2009300390B2 (en) * | 2008-09-30 | 2015-05-14 | SpecGx LLC | Processes for the production of buprenorphine with reduced impurity formation |
| GB2591302A (en) * | 2020-01-27 | 2021-07-28 | Azad Pharma Ag | Process for the synthesis of buprenorphine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1136214A (en) * | 1965-06-15 | 1968-12-11 | Reckitt & Sons Ltd | Thebaine and oripavine derivatives |
| US3474101A (en) * | 1960-09-05 | 1969-10-21 | Reckitt & Sons Ltd | Thebaine and oripavine derivatives |
| FR2554816B1 (en) * | 1983-11-16 | 1986-09-26 | Sanofi Sa | NEW NORORIPAVIN DERIVATIVE HAVING BOTH AGONIST AND ANTAGONIST ACTIVITY OF MORPHINIC RECEPTORS |
| DE3885592D1 (en) * | 1987-07-06 | 1993-12-16 | Basf K & F Corp | METHOD FOR PRODUCING NATURAL METHYL ANTHRANILATE. |
| EP0912577A2 (en) * | 1996-05-21 | 1999-05-06 | THE UNITED STATES OF AMERICA, as represented by the Secretary of the Department of Health and Human Services | Novel methods of o-demethylation and n-deprotection |
-
2002
- 2002-05-10 GB GB0210638A patent/GB2388369B/en not_active Revoked
-
2003
- 2003-04-24 CA CA2484985A patent/CA2484985C/en not_active Expired - Fee Related
- 2003-04-24 ES ES03749946T patent/ES2252687T3/en not_active Expired - Lifetime
- 2003-04-24 WO PCT/GB2003/001735 patent/WO2003095458A1/en not_active Application Discontinuation
- 2003-04-24 AT AT03749946T patent/ATE307816T1/en not_active IP Right Cessation
- 2003-04-24 EP EP03749946A patent/EP1504011B1/en not_active Expired - Lifetime
- 2003-04-24 DE DE60302061T patent/DE60302061T2/en not_active Expired - Lifetime
- 2003-04-24 US US10/512,746 patent/US7267968B2/en not_active Expired - Fee Related
- 2003-04-24 AU AU2003226563A patent/AU2003226563A1/en not_active Abandoned
-
2009
- 2009-12-23 AU AU2009251172A patent/AU2009251172A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1504011A1 (en) | 2005-02-09 |
| EP1504011B1 (en) | 2005-10-26 |
| US7267968B2 (en) | 2007-09-11 |
| AU2003226563A1 (en) | 2003-11-11 |
| AU2009251172A1 (en) | 2010-01-21 |
| ES2252687T3 (en) | 2006-05-16 |
| CA2484985A1 (en) | 2003-11-20 |
| GB2388369B (en) | 2004-05-05 |
| GB0210638D0 (en) | 2002-06-19 |
| DE60302061T2 (en) | 2006-07-27 |
| GB2388369A (en) | 2003-11-12 |
| US20050164358A1 (en) | 2005-07-28 |
| WO2003095458A1 (en) | 2003-11-20 |
| ATE307816T1 (en) | 2005-11-15 |
| CA2484985C (en) | 2011-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| R081 | Change of applicant/patentee |
Ref document number: 1504011 Country of ref document: EP Owner name: RB PHARMACEUTICALS LIMITED, GB Free format text: FORMER OWNER: RECKITT BENCKISER HEALTHCARE (UK) LTD., SLOUGH, GB Effective date: 20120920 |
|
| R082 | Change of representative |
Ref document number: 1504011 Country of ref document: EP Representative=s name: BARDEHLE PAGENBERG PARTNERSCHAFT PATENTANWAELT, DE Effective date: 20120920 |